Oak Bluffs Vacation Rentals

Oak Bluffs is a beautiful peninsula on the north eastern coast of Martha’s Vineyard that is bordered by Nantucket Sound. Renting a vacation home in Oak Bluffs gives you so many options. Our list of vacations rentals include luxury waterfront properties with exceptional views of the sound and quaint Victorian homes that allow you to glimpse deeply into Martha’s Vineyard’s historic past. Vacationing in Oak Bluffs is like taking a trip back in time. Ocean air and private beaches make you feel as though you have Martha’s Vineyard all to yourself.

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Hart Haven, Spacious Contemporary Colonial, Private Association Beach .8 mi from house, Private Association Tennis, 5 min walk from house

Located in the desirable enclave of homes known as Hart Haven just on the outskirts of Oak Bluffs Center, rental guests will surely enjoy this beautifully maintained home bordered by...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$10,000 - $12,000
June 2026
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July 2026
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 $10,000
August 2026
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$10,000
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 $10,000
September 2026
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$10,000
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 $10,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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PEMBT

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Property Details
Oak Bluffs Vacation Retreat – Exceptional Craftsmanship, Thoughtful Design & Unmatched Comfort, Sleep 8

Custom crafted with extraordinary attention to detail, quality, and comfort, this stunning Oak Bluffs vacation home offers an exceptional island getaway. Nestled in a peaceful residential neighborhood just two miles...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
3
Baths: 
3
Price Range:
$4,500 - $12,000
June 2026
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July 2026
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 $11,000
August 2026
SuMoTuWeThFrSaWeek
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$11,000
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 $9,000
September 2026
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$6,500
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$5,500
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 $5,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
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PIN15

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Property Details
Beautiful Oak Bluffs Home, Screened Porch & Open Porch, Association Tennis Courts, 4 bedrooms, 3.5 baths, Ideally Located just 2 miles to Town and Beach

Spacious contemporary home nestled in the lovely community of homes Meadow View Farms just on the outskirts of Oak Bluffs and 2 miles to town center and Oak Bluffs beaches....Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$9,750 - $11,750
June 2026
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July 2026
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$11,750
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 $11,750
August 2026
SuMoTuWeThFrSaWeek
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$11,750
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 $11,750
September 2026
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$9,750
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 $9,750
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
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GOLDF

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Property Details
Outstanding Oak Bluffs Summer Home with Heated Pool and Patio Surround, Screened Porch with Living and Dining Area, Association Tennis Courts.

MVVR Exclusive Listing:  Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful getaway yet is just a short drive to the...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
5
Baths: 
3
Price Range:
$5,500 - $11,500
June 2026
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July 2026
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$10,500
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 $11,000
August 2026
SuMoTuWeThFrSaWeek
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$11,000
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 $9,000
September 2026
SuMoTuWeThFrSaWeek
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$5,500
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 $5,500
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

Pool Heated to 80 July & August and the 1st week in September included in the rental rate!

 

Pool Heated to 80  May, June & September weeks at additional cost ($400). 

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HOL14

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Property Details
Gorgeous Waterfront Home on the Lagoon Oak Bluffs, Kayak, Swim, Enjoy the Sunsets, 4 bedrooms 4.5 Baths

Stunning Waterfront home nestled just in the outskirts of Oak Bluffs, 1 mile from the town center and Oak Bluffs beaches. This home offers 150 feet of private lagoon beach,...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$5,000 - $10,500
June 2026
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July 2026
SuMoTuWeThFrSaWeek
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 $16,500
August 2026
SuMoTuWeThFrSaWeek
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$16,500
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 $10,500
September 2026
SuMoTuWeThFrSaWeek
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$10,500
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$9,000
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$7,000
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$7,000
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 $5,000
Clean Fee: 
$750 per week
Tax: State & Local: 
11.7
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GLEDE

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Property Details
Stunning New Custom Luxury Home, Oak Bluffs, 18 x 36 Heated Saltwater Pool, Bluestone Patio, 4 Bedrooms 3.5 baths

Tucked just beyond the heart of downtown Oak Bluffs, this spacious, architect-designed retreat offers families and friends an exceptional Vineyard vacation experience.

Thoughtfully crafted by a noted architect, the home...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$9,000 - $10,000
June 2026
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July 2026
SuMoTuWeThFrSaWeek
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$16,500
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$18,000
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$18,000
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 $20,000
August 2026
SuMoTuWeThFrSaWeek
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$20,000
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$20,000
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$21,000
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$21,500
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$18,000
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 $10,000
September 2026
SuMoTuWeThFrSaWeek
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$10,000
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$10,000
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$10,000
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$9,000
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 $9,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7

1st Two Weeks of July 2026 being offered at $16,500 per week

 

Pool Heated to 81 degrees July & August included in Rental Rate

Pool Heated to 81 degrees June & September additional $300 Propane Surcharge

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WEI81

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Property Details
Lovely Oak Bluffs Escape, 3 Bedrooms in Main House, 2 Bedrooms over Garage, 3.5 Baths Multiple Living Spaces, Walk to Oak Bluffs Center, 1 Mile

Nestled on a tranquil cul-de-sac in the heart of Oak Bluffs, this meticulously renovated Modern Colonial offers a special Martha's Vineyard experience. Thoughtfully reimagined in 2025, the property encompasses a...Read more

Location: 
Oak Bluffs
Sleeps: 
10
Bedrooms: 
5
Baths: 
3
Price Range:
$7,000 - $10,000
June 2026
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July 2026
SuMoTuWeThFrSaWeek
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$9,000
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$10,000
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 $10,000
August 2026
SuMoTuWeThFrSaWeek
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$10,000
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$12,000
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$14,000
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$12,000
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$10,000
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 $10,000
September 2026
SuMoTuWeThFrSaWeek
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$10,000
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$7,000
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$7,000
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$7,000
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 $7,000
Clean Fee: 
$650 per week
Tax: State & Local: 
11.7
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CURRM

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Property Details
Outstanding Designer Home, 15 Min Walk to Oak Bluffs Center, 4 Bedrooms each en suite with TV, Occupancy Limit 9

Stylish Dreamy Home on Dreamer's Way, less than a mile from the town center and beach area! The owners have left nothing out in the way of design and comfort in...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
4
Baths: 
4
Price Range:
$3,500 - $9,900
June 2026
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July 2026
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$8,700
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$8,900
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$9,200
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 $9,400
August 2026
SuMoTuWeThFrSaWeek
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$9,400
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$10,700
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$11,200
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$10,700
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$9,500
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 $8,200
September 2026
SuMoTuWeThFrSaWeek
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$8,200
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$6,600
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$5,600
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$4,600
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 $4,300
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7

Owner ACCEPTS 3 NIGHT MINIMUM STAYS, MEMORIAL DAY WEEKEND TO JUNE 16TH, AND SEPT 7TH TO THE END OF OCTOBER.

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VANA2

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Property Details
Charming , Modern In-Town Oak Bluffs Vacation Home. Walk to Town, Parks, Beach. 4 Bedrooms, Sleeps 8, 3 Baths

This charming Oak Bluffs home is tucked away in a peaceful neighborhood, yet conveniently located just a 10-minute walk to the heart of town, the harbor, and the beach. Meticulously...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$4,500 - $9,000
June 2026
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August 2026
SuMoTuWeThFrSaWeek
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$8,500
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$6,500
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Clean Fee: 
$450 per week
Tax: State & Local: 
11.7
Add Favorite
 
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NORM2

Inquire
Property Details
Gorgeous Waterfront Home on the Lagoon, Newly Renovated, 4 bedrooms, 3.5 Baths, Spectacular Waterviews, Upper & Lower Decks

Waterfront Retreat on the Lagoon – Oak Bluffs

This beautifully renovated waterfront home offers breathtaking views, a private sandy beach on the Lagoon, and a stylish, coastal-inspired interior. Nearly every room...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$6,500 - $9,000
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$12,900
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$14,500
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$15,000
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 $15,000
August 2026
SuMoTuWeThFrSaWeek
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$15,000
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$17,000
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$17,000
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$17,000
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$17,000
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 $13,000
September 2026
SuMoTuWeThFrSaWeek
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$13,000
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$9,000
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$8,000
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$8,000
27
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29
30
 $6,500
Clean Fee: 
$600
Tax: State & Local: 
11.7
Add Favorite
 
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CORAG

Inquire
Property Details
Lovely, Newly Updated Oak Bluffs Home. Multiple Indoor/Outdoor Living/Lounge Areas, Sleeps 8, 10/15 minute Walk to the Vilage Center.

Note: All photos are virtually staged photos by the owner, all new furnishings will be arriving throughout the winter months. 

Welcome to Noble House, a beautifully updated home nestled in a charming neighborhood just...Read more

Location: 
Oak Bluffs
Sleeps: 
9
Bedrooms: 
3
Baths: 
2
Price Range:
$4,500 - $8,800
June 2026
SuMoTuWeThFrSa
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July 2026
SuMoTuWeThFrSaWeek
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$7,700
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$7,700
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$7,700
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 $9,000
August 2026
SuMoTuWeThFrSaWeek
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$9,000
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$9,000
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$9,000
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$8,500
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$8,800
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 $8,200
September 2026
SuMoTuWeThFrSaWeek
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$8,200
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$6,500
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$5,500
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$4,500
27
28
29
30
 
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7
Add Favorite
 
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POWDA

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Property Details
Beautiful Newly Updated Oak Bluffs Home, Nestled on a Large Landscaped Lot in a Quiet Enclave of Homes. 4 Bedrooms. 4.5 Baths

Step inside to discover a welcoming interior, highlighted by a sunroom featuring comfortable seating around the TV. The open first-floor plan seamlessly integrates the main family room complete with a media...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
4
Price Range:
$6,000 - $8,500
June 2026
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July 2026
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$8,500
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$8,500
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$9,000
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 $9,000
August 2026
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$9,000
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$12,000
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$12,000
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$11,500
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$9,000
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 $7,000
September 2026
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$7,000
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$6,000
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$6,000
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$6,000
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 $6,000
Clean Fee: 
$600 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BOWDL

Inquire
Property Details
Lovely Custom Contemporary Home, Tucked in the Community of Bayes Hill, 4 Bedrooms, 4 Bath, Landscaped, Deck, Patio Dining Area

Designed with a sophisticated contemporary aesthetic, this chic vacation retreat showcases an open floor plan, expansive windows, and beautifully curated interiors. Offering four bedrooms and 3.5 baths, the home is...Read more

Location: 
Oak Bluffs
Sleeps: 
8
Bedrooms: 
4
Baths: 
3
Price Range:
$7,000 - $8,050
June 2026
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July 2026
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$7,750
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$7,750
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$7,750
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 $8,050
August 2026
SuMoTuWeThFrSaWeek
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$8,050
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$8,050
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$8,050
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$8,050
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$8,050
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 $8,050
September 2026
SuMoTuWeThFrSaWeek
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$8,050
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$7,500
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$7,500
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$7,500
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 $7,500
Clean Fee: 
$500 per week
Tax: State & Local: 
11.7
Add Favorite
 
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BEG21

Inquire
Property Details
Ideally located just 1 mile to OB Center, Many Updates, Enclosed Private Back Yard, Deck Nicely outfitted with Dining and new Living Area Grouping., Central AC

This cozy recently updated vacation home is tucked on a quiet street just on the outskirts of Oak Bluffs Center. Bike or walk to the town center, Inkwell Beach, and the picturesque Harbor...Read more

Location: 
Oak Bluffs
Sleeps: 
6
Bedrooms: 
3
Baths: 
2
Price Range:
$4,500 - $8,000
June 2026
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July 2026
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$7,000
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$7,000
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$7,000
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 $7,000
August 2026
SuMoTuWeThFrSaWeek
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$7,000
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$8,000
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$8,000
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$8,000
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$8,000
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 $4,500
September 2026
SuMoTuWeThFrSaWeek
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$4,500
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$4,500
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$4,500
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$4,500
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 $4,500
Clean Fee: 
$400 per week
Tax: State & Local: 
11.7

Note: Owner maintains security camera on front of house

Add Favorite
 
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CASHK

Inquire
Property Details
Lovely Home, Centrally Located, Bike Paths, AC all Rooms

This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window AC in all rooms, and a well-equipped modern kitchen. The home is nicely situated...Read more

Location: 
Oak Bluffs
Sleeps: 
5
Bedrooms: 
3
Baths: 
2
Price Range:
$7,500 - $7,800
June 2026
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July 2026
SuMoTuWeThFrSaWeek
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$7,500
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$7,500
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$7,500
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 $7,500
August 2026
SuMoTuWeThFrSaWeek
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$7,500
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$7,800
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$7,800
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$7,800
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$7,800
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September 2026
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Clean Fee: 
$325 per week
Tax: State & Local: 
11.7

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